Synthesis of <sup>18</sup>F-Labeled Aryl Fluorosulfates via Nucleophilic Radiofluorination
Young‐Do Kwon, Min Ho Jeon, Nam Kyu Park, Jeong Kon Seo, Jeongmin Son, Young Hoon Ryu, Sung You Hong, Joong‐Hyun Chun
Abstract
Sulfuryl fluoride gas is a key reagent for SO2F transfer. However, conventional SO2F transfer reactions have limited 18F-radiochemistry translation, due to the inaccessibility of gaseous [18F]SO2F2. Herein, we report the first SO2F2-free synthesis of aryl [18F]fluorosulfates from both phenolic and isolated aryl imidazylate precursors with cyclotron-produced 18F–. The radiochemical yields ranged from moderate to good with excellent functional group tolerance. The reliability of our approach was validated by the automated radiosynthesis of 4-acetamidophenyl [18F]fluorosulfate.
Topics & Concepts
ChemistryArylNucleophileCombinatorial chemistryMedicinal chemistryStereochemistryOrganic chemistryCatalysisAlkylFluorine in Organic ChemistryClick Chemistry and ApplicationsSynthesis and Reactions of Organic Compounds